Rapid screening of environmental chemicals for estrogen receptor binding capacity

Environmental Health Perspectives

Volumn 106, Issue 9, 1998, Pages 551-557

  Bolger, Randall ^a   Wiese, Thomas E ^b   Ervin, Kerry ^a   Nestich, Scott ^a   Checovich, William ^a  

^a INVITROGEN CORPORATION   (United States)

^b UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

Competition binding; Endocrine disruptor screening; Estrogen; Estrogen receptor; Fluorescence polarization

Indexed keywords

ENVIRONMENTAL CHEMICAL; ESTROGEN RECEPTOR; INDUSTRIAL CHEMICAL; RADIOLIGAND;

ARTICLE; ENDOCRINE FUNCTION; ENVIRONMENTAL TEMPERATURE; FLUORESCENCE POLARIZATION; PRIORITY JOURNAL; RECEPTOR BINDING; SCREENING; SOLUBILITY; TEMPERATURE; WILDLIFE;

EID: 0031762676     PISSN: 00916765     EISSN: None     Source Type: Journal    
DOI: 10.1289/ehp.98106551     Document Type: Article

References (75)

1. Colborn T, vom Saal FS, Soto AM. Developmental effects of endocrine-disrupting chemicals In wildlife and humans. Environ Health Perspect 101:378-384(1993).
2. Colborn T. Environmental estrogens: health implications for humans and wildlife. Environ Health Perspect 103(suppl 7):135-136 (1995).
3. Colborn T, Dumanoski D, Myers JP. Our Stolen Future: Are We Threatening Our Fertility, Intelligence, and Survival? - A Scientific Detective Story. New York:Dutton, 1996.
4. Harrison PTC, Holmes P, Humfrey CDN. Reproductive health in humans and wildlife: are adverse trends associated with environmental chemical exposure. Sci Total Environ 205:97-106 (1997).
5. Davis DL, Bradlow HL, Wolff M, Woodruff T, Hoel DG, Anton-Culver H, Medical hypothesis: xenoestrogens as preventable causes of breast cancer. Environ Health Perspect 101:372-377 (1993).
6. Toppari J, Larsen JC, Christiansen P, Giwercman A, Grandjean P, Guillette LJ Jr, Jégou B, Jensen TK, Jouannet P, Keiding N, et al. Male reproductive health and environmental xenoestrogens. Environ Health Perspect 104(suppl 4):741-803 (1996).
7. Thomas K, Colborn T. Organochlorine endocrine disruptors in human tissues. In: Chemically-Induced Alterations in Sexual and Functional Development: The Wildlife/Human Connection (Colborn T, Clement C, eds). Princeton, NJ:Princeton Scientific Publishing, 1992:365-395.
8. Coussens R, Sierens G. Oestrogenic properties of tulip bulbs. Arch Int Pharmacodyn 78:309-312 (1949).
9. Marselos M, Tomatis L, Diethylstilbestrol I: Pharmacology, toxicology and carcinogenicity in humans. Eur J Cancer 28A:1182-1189 (1992).
10. Guzelian PS. Comparative toxicology of chlordecone (Kepone) in humans and experimental animals. Annu Rev Pharmacol Toxicol 22:89-113 (1982).
11. Gallert RJ. Kepone, mirex, dieldrin, and aldrin: estrogenic activity and the induction of persistent vaginal estrus and anovulation in rats following neonatal treatment. Environ Res 16:138 (1978).
12. Nelson JA, Struck RF, James R. Estrogenic activities of chlorinated hydrocarbons. J Toxicol Environ Health 4:325-339 (1978).
13. Fry DM, Toone CK, DDT-induced feminization of gull embryos, Science 213:922-924 (1981).
14. Kelce WR, Wilson EM. Environmental antiandrogens: developmental effects, molecular mechanisms, and clinical implications, J Mol Med 75:198-207 (1997).
15. McLachlan JA, Wong A, Degen GH, Barren JC. Morphologic and neoplastic transformation of Syrian hamster embryo fibroblasts by diethylstilbestrol and its analogs. Cancer Res 42:3040-3045 (1982).
16. Kavlock RJ, Daston GP, DeRosa C, Fenner-Crisp P, Gray LE, Kaattari S, Lucier G, Luster M, Mac MJ, Maczka C, et al. Research needs for the risk assessment of health and environmental effects of endocrine disrupters: a report of the US EPA-sponsored workshop. Environ Health Perspect 104(suppl 4):715-740 (1996).
17. Kavlock RJ, Ankley GT. A perspective on the risk assessment process for endocrine-disruptive effects on wildlife and human health. Risk Anal 16:731-739 (1996).
18. Ashby J. A hierarchical approach to the evaluation of chemicals for estrogenic and other endocrine-disrupting properties. Environ Toxicol Pharmacol 3:87-90 (1997).
19. Korach KS, McLachlan JA. Techniques for detection of estrogenicity. Environ Health Perspect 103(suppl 71:5-8 (1995).
20. Reel JR, Lamb JC IV, Neal BH. Survey and assessment of mammalian estrogen biological assays for hazard characterization, Fundam Appl Toxicol 34:288-305 (1996).
21. Zacharewski T. In vitro bioassays for assessing estrogenic substances. Environ Sci Technol 31:613-623 (1997).
22. Gray LE, Kelce WR, Wiese T, Tyl R, Gaido K, Cook J, Klinefelter G, Desaulniers D, Wilson E, Zacharewski T, et al. Endocrine screening methods workshop report: detection of estrogenic and androgenic hormonal and antihormonal activity for chemicals that act via receptor or steroidogenic enzyme mechanisms. Reprod Toxicol 11:719-750 (1997).
23. Gellert RJ. Uterotrophic activity of polychlorinated biphenyls (PCB) and induction of precocious reproductive aging in neonatelly treated female rats. Environ Res 16:123-130 (1978).
24. Hammond B, Katzenellenbogen BS, Krauthammer N, McConnell J, Estrogenic activity of the insecticide chlordecone (Kepone) and interaction with uterine estrogen receptors, Proc Natl Acad Sci USA 76:6641-6645 (1979).
25. Kupfer D, Bulger WH, Metabolic activation of pesticides with proestrogenic activity. Fed Proc 46:1864-1869 (1987).
26. Krishnan AV, Stathis P, Permuth SF, Tokes L, Feldman D. Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 132:2279-2286 (1993).
27. White R, Jobling S, Hoare SA, Sumpter JP, Parker MG, Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135:175-182 (1994).
28. Newbold R. Cellular and molecular effects of developmental exposure to diethylstilbestrol: implications for other environmental estrogens. Environ Health Perspect:103(suppl 7):83-87 (1995).
29. Katzenellenbogen JA. The structural pervasiveness of estrogenic activity. Environ Health Perspect 103(suppl 7):99-101(1995).
30. Nimrod AC, Benson WH. Environmental estrogenic effects of alkylphenol ethoxylates. Crit Rev Toxicol 26:335-364 (1996).
31. Green S, Chambon P. The oestrogen receptor: from perception to mechanism. In: Nuclear hormone receptors: molecular mechanisms, cellular functions, clinical abnormalities (Parker MG, ed). London:Academic Press, 1991:15-38.
32. Parker MG, Arbuckle N, Dauvois S, Danielian P, White R. Structure and function of the estrogen receptor. Ann NY Acad Sci 684:119-126 (1993).
33. Tsai MJ, O'Malley BW. Molecular mechanisms of action of steroid/thyroid receptor superfamily members. Ann Rev Biochem 63:451-486 (1994).
34. Smith DF, Toft DO. Steroid receptors and their associated proteins. Mol Endocrinol 7:4-11 (1993).
35. Landel CC, Kushner PJ, Greene GL Estrogen receptor accessory proteins: Effects on receptor-DNA interactions. Environ Health Perspect 103(suppl 7):232-238 (1995).
36. Beekman JM, Allan GF, Tsai SY, Tsai MJ, O'Malley BW. Transcriptional activation by the estrogen receptor requires a conformational change in the ligand binding domain. Mol Endocrinol 7:1266-1274 (1993).
37. Jordan VC. Molecular mechanisms of antiestrogen action in breast cancer. Breast Cancer Res Treat 31:41-52 (1994).
38. Grainger OJ, Metcalfe JC. Tamoxifen: teaching an old drug new tricks? Nat Med 2:381-385 (1996).
39. Paech K, Webb P, Kuiper G, Nilsson S, Gustafsson JA, Kushner PJ, Scanlan TS. Differential ligand activation of estrogen receptors ER-alpha and ER-beta at AP1 sites. Science 277:1508-1510 (1997).
40. Stancel GM, Boettger-Tong HL, Chiappetta C, Hyder SM, Kirkland JL, Murthy L, Loose-Mitchell DS. Toxicity of endogenous and environmental estrogens: what is the role of elemental interactions? Environ Health Perspect:103(suppl 7):29-33 (1995).
41. McLachlan JA. Functional toxicology: a new approach to detect biologically active xenobiotics. Environ Health Perspect 101:386-387 (1993).
42. Van Aswegen CH, Purdy RH, Wittliff JL, Binding of 2-hydroxyestradiol and 4-hydroxyestradiol to estrogen receptors from human breast cancers. J Steroid Biochem 32:485-492 (1989).
43. Shelby MD, Newbold RR, Tully DB, Chae K, Davis VL Assessing environmental chemicals for estrogenicity using a combination of in vitro and in vivo assays, Environ Health Perspect 104:1296-1300 (1996).
44. Cook ND, Scintillation proximity assay: a versatile high-throughput screening technology. Drug Discovery Today 1:287-294 (1996).
45. Checovich WJ, Bolger RE, Burke T. Fluorescence polarization - a new tool for cell and molecular biology. Nature 375:254-256 (1995).
46. Perrin F. Polarisation de la lumiere de fluorescence vie moyenne des molecules dans líetat excite. J Phys Radium 7:390-401 (1926).
47. Weber G. Fluorescence and Phosphorescence Analysis. New York:Wiley, 1966.
48. Dandliker WB, Hsu ML, Levin J, Rao BR. Equilibrium and kinetic inhibition assays based upon fluorescence polarization. Methods Enzymol 74:3-28 (1981).
49. Jameson DM, Sawyer WH. Fluorescence anisotropy applied to biomolecular interactions. Methods Enzymol 246:283-300 (1995).
50. Lundblad JR, Laurance M, Goodman RH. Fluorescence polarization analysis of protein-DNA and protein-protein interactions. Mol Endocrinol 10:607-612 (1996).
51. Hwang KJ, Carlson KE, Anstead GM, Katzenellenbogen JA. Donor-acceptor tetrahydrochrysenes, inherently fluorescent, high-affinity ligands for the estrogen receptor: binding and fluorescence characteristics and fluorometric assay of receptor. Biochemistry 31:11536-11545 (1992).
52. Brown M, Sharp PA. Human estrogen receptor forms multiple protein-DNA complexes. J Biol Chem 265:11238-11243 (1990).
53. Obourn JO, Koszewski NJ, Notides AC. Hormone- and DNA-binding mechanisms of the recombinant human estrogen receptor. Biochemistry 32:6229-6236 (1993).
54. Cheskis BJ, Karathenasis S, Lyttle CR. Estrogen receptor ligands modulate its interaction with DNA. J Biol Chem 272:11384-11391 (1997).
55. Ozers MS, Hill JJ, Ervin K, Wood JR, Nardulli AM, Rover CA, Gorski J. Equilibrium binding of estrogen receptor with DNA using fluorescence anisotropy. J Biol Chem 272:30405-30411 (1997).
56. Waller CL, Juma BW, Gray LE, Kelce WR. Three-dimensional quantitative structure-activity relationships for androgen receptor ligands. Toxicol Appl Pharmacol 137:219-227 (1996).
57. Kenakin TP. Radiolabeled binding experiments. In: Pharmacologic Analysis of Drug/Receptor Interaction. NewYork:Raven, 1993;385-410.
58. Swillens S. Interpretation of binding curves obtained with high receptor concentrations: practical aid for computer analysis. Mol Pharmacol 47:1197-1203 (1995).
59. Munson PJ, Rodbard D. An exact correction to the "Cheng-Prusoff" correction. J Recept Res 8:533-546 (1988).
60. Clark J, Scrader W, O'Malley B. Mechanisms of Action of Steroid Hormones. Philadelphia, PA:WB Saunders Company, 1992.
61. Soto AM, Sonnenschein C, Chung KL, Fernandez MF, Olea N, Serrano FO. The E-SCREEN assay as a tool to identify estrogens: an update on estrogenic environmental pollutants. Environ Health Perspect 103(suppl 7):113-122 (1995).
62. Harris CA, Henttu P, Parker MG, Sumpter JP. The estrogenic activity of phthalate esters in vitro. Environ Health Perspect 105:802-811 (1997).
63. Waller CL, Oprea Tl, Chae K, Park H-K, Korach KS, Laws SC, Wiese TE, Kelce WR, Gray LE. Ligand-based identification of environmental estrogens. Chem Res Toxicol 9:1240-1248 (1996).
64. Kuiper GGJM, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, Gustafsson JA, Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology 138:863-870 (1997).
65. Ramamoorthy K, Wang F, Chen IC, Morris JD, McDonnell DP, Leonard LS, Gaido KW, Bocchinfuso WP, Korach KS, Safe S. Estrogenic activity of a dieldrin/toxaphene mixture in the mouse uterus, MCF-7 human breast cancer cells, and yeast-based estrogen receptor assays: no apparent synergism. Endocrinology 138:1520-1527 (1997).
66. Wade MG, Desaulniers D, Leingartner K, Foster WG. Interactions between endosulfan and dieldrin on estrogen-mediated processes in vitro and in vivo, Reprod Toxicol 11:791-798 (1997).
67. Gaido KW, Leonard LS, Lovell S, Gould JC, Babai D, Portier CJ, McDonnell DP. Evaluation of chemicals with endocrine modulating activity in a yeast-based steroid hormone receptor gene transcription assay. Toxicol Appl Pharmacol 143:205-212 1997).
68. Wiese TE, Polin LA, Palomino E, Brooks SC. Induction of the estrogen specific mitogenic response of MCF-7 cells by selected analogues of estradiol-17β: a 3D QSAR study. J Med Chem 40:3659-3669 (1997).
69. McBlain WA. The levo enantiomer of o,p'-DDT inhibits the binding of 17 beta-estradiol to the estrogen receptor. Life Sci 40:215-221 (1987).
70. Soto AM, Chung KL, Sonnenschein C. The pesticides endosulfan, toxaphene, and dieldrin have estrogenic effects on human estrogen-sensitive cells. Environ Health Perspect 102:380-383 (1994).
71. Dodds EC, Lawson W. Molecular structure in relation to oestrogenic activity. Compounds without a phenanthrene nucleus, Proc R Soc Lond B 125:222-232 (1938).
72. Steinmetz R, Brown NG, Allen DL, Bigsby RM, Benjonathan N. The environmental estrogen bisphenol A stimulates prolactin release in vitro and in vivo. Endocrinology 138:1780-1786 (1997).
73. Le Drean Y, Kern L, Pakdel F, Valotaire Y. Rainbow trout estrogen receptor presents an equal specificity but a differential sensitivity for estrogens than human estrogen receptor. Mol Cell Endocrinol 109:27-35 (1995).
74. Arnold SF, Klotz DM, Collins BM, Vonier PM, Guillette LJ, McLachlan JA, Synergistic activation of estrogen receptor with combinations of environmental chemicals. Science 272:1489-1492 (1996).
75. Jobling S, Reynolds T, White R, Parker MG, Sumpter JP. A variety of environmentally persistent chemicals, including some phthalate plasticizers, are weakly estrogenic. Environment Health Perspect 582-587 (1995).